1. Field of the Invention
The present invention provides novel diazepinoindole compounds of Formula I. These compounds are 5-HT ligands and are useful for treating diseases wherein modulation of 5-HT activity is desired.
2. Technology Description
Serotonin has been implicated in a number of diseases and conditions that originate in the central nervous system. These include diseases and conditions related to sleeping, eating, perceiving pain, controlling body temperature, controlling blood pressure, depression, anxiety, schizophrenia, and other bodily states. Serotonin also plays an important role in peripheral systems, such as the gastrointestinal system, where it has been found to mediate a variety of contractile, secretory, and electrophysiologic effects.
As a result of the broad distribution of serotonin within the body, there is a tremendous interest in drugs that affect serotonergic systems. In particular, agonists, partial agonists and antagonists are of interest for the treatment of a wide range of disorders, including anxiety, depression, hypertension, migraine, obesity, compulsive disorders, schizophrenia, autism, neurodegenerative disorders (e.g. Alzheimer""s disease, Parkinsonism, and Huntington""s chorea), and chemotherapy-induced vomiting.
The major classes of serotonin receptors (5-HT1-7) contain fourteen to eighteen separate receptor subtypes that have been formally classified. See Glennon, et al., Neuroscience and Behavioral Reviews, 1990, 14, 35; and D. Hoyer, et al. Pharmacol. Rev. 1994, 46, 157-203.
For example, the 5-HT2 family of receptors is comprised of 5-HT2A, 5-HT2B, and 5-HT2C subtypes, which have been grouped together on the basis of primary structure, secondary messenger system, and operational profile. All three subtypes are G-protein coupled, activate phospholipase C as a principal transduction mechanism, and contain a seven-transmembrane domain structure. There are distinct differences in the distribution of the three 5-HT2 subtypes. The 5-HT2B and 5-HT2A receptors are widely distributed in the periphery, while the 5-HT2C receptor has been found only in the central nervous system, being highly expressed in many regions of the human brain. See G. Baxter, et al. Trends in Pharmacol. Sci. 1995, 16, 105-110.
Subtype 5-HT2A has been associated with effects including vasoconstriction, platelet aggregation, and bronchoconstriction, while subtype 5-HT2C has been associated with diseases that include depression, anxiety, obsessive compulsive disorder, panic disorders, phobias, psychiatric syndromes, and obesity. Very little is known about the pharmocologic role of the 5-HT2B receptor. See F. Jenck, et al., Exp. Opin. Invest. Drugs, 1998, 7, 1587-1599; M. Bos, et al., J. Med. Chem., 1997, 40, 2762-2769; J. R. Martin, et al., The Journal of Pharmacology and Experimental Therapeutics, 1998, 286, 913-924; S. M. Bromidge, et al., J. Med. Chem., 1998, 41, 1598-1612; G. A. Kennett, Drugs, 1998, 1, 4, 456-470; and A. Dekeyne, et al., Neuropharmacology, 1999, 38, 415-423.
The following references possibly suggest molecules containing both indole groups and cyclic rings wherein the indolyl nitrogen atom and an additional nitrogen atom form a part of the cyclic ring: SU 460724 and U.S. Pat. No. 4,673,674. However, the molecules described in the above-described references contain additional substituents that the inventors of the instant invention have discovered are not required, and potentially not desired. U.S. Pat. No. 4,210,590 suggests the reduction of indole compounds to indoline compounds to yield compounds having biological and/or pharmacological properties. U.S. Pat. Nos. 3,689,503 and 3,867,374 disclose 2,3,4,5-tetrahydro-1H-[1,4]-diazepino [1,2-a]indole compounds and their use in treating central nervous system diseases or disorders.
Despite the above teachings, there is currently a need for pharmaceutical agents that are useful in treating diseases and conditions that are associated with 5-HT receptors.
In accordance with the present invention novel compounds which demonstrate useful biological activity, and particularly activity as 5-HT receptor ligands are provided. More specifically, the compounds are unsubstituted or substituted 2,3,4,5-tetrahydro-1H-[1,4]-diazepino[1,7-a]indoles.
A first embodiment of the present invention provides compounds of formula I:
A compound of formula I: 
where a is a single bond or double bond, and where
R1a, R1b, R2a and R2b are each independently
(a) H, Cl, Br, I, F, CN, CF3, OCF3, OR5, CONR5R6, COR5, CO2R5, Y(CH2)mXR5 or YC(O)(CH2)mXR5, where m=0-3, Yxe2x95x90CH2, S, O, or NR6, Xxe2x95x90CH2, S, O, NR6;
(b) (CH2)pAr where p=0-3 and Ar is aryl or heteroaryl optionally substituted with one or more of the following: H, halogen, CN, NO2, OR7, CF3, OCF3, SR7, SO2R7, SO2NR7R8, NR7R8, CONR7R8, NR7COR8, NR7CONR8R9, CO2R7, COR7, COR7, or R7; or
(c) linear or branched C1-C8 alkyl, linear or branched C2-C8 alkenyl, linear or branched C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, or C3-C8 cycloalkynyl; wherein any of these groups may be optionally substituted with one or more of the following: halogen, CN, NO2, COR7, OR7, NR7R8, SR7, CO2R7, CONR7R8 or NR7COR8; and where
R3 is
(a) H, Cl, Br, I, F, CN, CF3, OCF3, alkyl, Ar, OR5, SR5, CHO, CONR5R6, COR5, CO2R5, (Y)o(CH2)nXR5, C(O)C(O)XR5, (Y)o(CH2)nC(O)XR5, C(O)(CH2)nXR5, (Y)o(CH2)nN(R6)C(O)R5, (Y)o(CH2)nN(R6)S(O)2R5, (Y)o(CH2)nN(R6)C(O)OR5, (Y)o(CH2)nN(R6)C(O)NR5R6 where o=0 or 1, n=0-3, Xxe2x95x90CH2, S, O, or NR6 and Yxe2x95x90CH2, S, O or NR6, where Ar is aryl or heteroaryl optionally substituted with one or more of the following: H, halogen, CN, NO2, OR7, CF3, OCF3, SR7, SO2R7, SO2NR7R8, NR7R8, CONR7R8, NR7COR8, NR7CONR8R9, CO2R7, COR7, or R7; or
(b) linear or branched C1-C8 alkyl, linear or branched C2-C8 alkenyl, linear or branched C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, or C3-C8 cycloalkynyl; wherein any of these groups may be optionally substituted with one or more of the following: halogen, CN, NO2, COR10, OR10, NR10R8, SR10, CO2R10, CONR10R8 or NR10COR8; and where
R4, R5 and R6 are each independently
(a) H, linear or branched C1-C8 alkyl, linear or branched C2-C8 alkenyl, linear or branched C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, or C3-C8 cycloalkynyl; wherein any of these groups other than H may be optionally substituted with one or more of the following: halogen, CN, NO2, COR10, OR10, NR10R11, SR10, CO2R10, CONR10R11 or NR10COR11; or where R5 and R6 are linked to form a 3 to 8 member ring; or
(b) (CH2)pAr where p=0-3 and Ar is aryl or heteroaryl optionally substituted with one or more of the following: H, halogen, CN, NO2, OR7, CF3, OCF3, SR7, SO2R7, SO2NR7R8, NR7R8, CONR7R8, NR7COR8, NR7CONR8R9, CO2R7, COR7, or R7; and where
R7, R8, and R9 are each independently
(a) H, linear or branched C1-C8 alkyl, linear or branched C2-C8 alkenyl, linear or branched C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, or C3-C8 cycloalkynyl groups, wherein any of these groups other than H may be optionally substituted with halogen, CN, NO2, COR10, OR10, NR10R11, SR10, CO2R10, CONR10R11, NR10COR11, NR10CONR11R12, or where R7, R8, or R9 are linked to form a ring; or
(b) (CH2)pAr where p=0-3 and Ar is aryl or heteroaryl optionally substituted with one or more of the following: H, halogen, CN, NO2, OR10, CF3, OCF3, SR10, SO2R10, SO2NR10R11, NR10R11, CONR10R11, NR10COR11, NR10CONR11R12, CO2R10, COR10, or R10; and where
R10, R11 and R12 are each independently H, linear or branched C1-C8 alkyl, linear or branched C2-C8 alkenyl, linear or branched C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, or C3-C8 cycloalkynyl;
or a stereoisomer or pharmaceutically acceptable salt thereof.
In particularly preferred embodiments, R1a, R1b, R2a, R2b and R4 are H and R3 is selected from either H, xe2x80x94C(O)C(O)XAr, xe2x80x94CH2C(O)XAr or xe2x80x94C(O)CH2XAr where X and Ar are as defined above.
Another embodiment of the present invention provides a pharmaceutical composition comprising a compound of formula I, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier. In preferred embodiments, the composition preferably comprises a therapeutically effective amount of the compound or salt.
Still another embodiment of the present invention provides a method for treating a disease or condition in a mammal (e.g. animal or human) wherein a 5-HT receptor is implicated and modulation of a 5-HT function is desired comprising administering to the mammal a therapeutically effective amount of a compound of formula I, or a pharmaceutically acceptable salt thereof.
Yet another embodiment of the present invention provides a method for treating or preventing diseases or disorders of the central nervous system comprising administering a therapeutically effective amount of a compound of formula I, or a pharmaceutically acceptable salt thereof to the mammal. Specific diseases or disorders for which the compound of formula I may have activity include, but are not limited to the following: obesity, depression, schizophrenia, a stress related disease, panic disorder, a phobia, obsessive compulsive disorder, post-traumatic-stress syndrome, immune system depression, incontinence, a stress induced problem with the urinary, gastrointestinal or cardiovascular system, neurodegenerative disorders, autism, chemotherapy-induced vomiting, hypertension, migraine headaches, cluster headaches, sexual dysfunction in a mammal, addictive disorder and withdrawal syndrome, an adjustment disorder, an age-associated learning and mental disorder, anorexia nervosa, apathy, an attention-deficit disorder due to general medical conditions, attention-deficit hyperactivity disorder, bipolar disorder, bulimia nervosa, chronic fatigue syndrome, conduct disorder, cyclothymic disorder, dysthymic disorder, fibromyalgia and other somatoform disorders, generalized anxiety disorder, an inhalation disorder, an intoxication disorder, a movement disorder, oppositional defiant disorder, a pain disorder, peripheral neuropathy, post-traumatic stress disorder, premenstrual dysphoric disorder, a psychotic disorder, seasonal affective disorder, a sleep disorder, a specific developmental disorder, and selective serotonin reuptake inhibition (SSRI) xe2x80x9cpoop outxe2x80x9d syndrome.
A further embodiment of the present invention comprises the use of a compound of formula (I) or a pharmaceutically acceptable salt thereof to prepare a medicament for treating or preventing diseases or disorders of the central nervous system.
A final embodiment of the present invention comprises a method for modulating 5-HT receptor function with an effective amount of a compound of formula I, or a pharmaceutically acceptable salt thereof.
An object of the present invention is to provide novel compounds having biological activity.
Still another object of the present invention is to provide a method for treating a disease or condition in a mammal wherein a 5-HT receptor is implicated and modulation of a 5-HT function is desired by using the novel compounds of the present invention.
A further object of the present invention is to provide a method for treating or preventing diseases of the central nervous system by using the novel compounds of the present invention.
These, and other objects, will readily be apparent to those skilled in the art as reference is made to the detailed description of the preferred embodiment.
In describing the preferred embodiment, certain terminology will be utilized for the sake of clarity. Such terminology is intended to encompass the recited embodiment, as well as all technical equivalents which operate in a similar manner for a similar purpose to achieve a similar result.
1. Terminology Definitions
The following definitions are used, unless otherwise described: halo is fluoro, chloro, bromo, or iodo. Alkyl, alkoxy, etc. denote both straight and branched groups; but reference to an individual group or moiety such as xe2x80x9cpropylxe2x80x9d embraces only the straight chain group or moiety, a branched chain isomer such as xe2x80x9cisopropylxe2x80x9d being specifically referred to. When alkyl can be partially unsaturated, the alkyl chain may comprise one or more (e.g. 1, 2, 3, or 4) double or triple bonds in the chain.
Aryl denotes a phenyl group or moiety or an ortho-fused bicyclic carbocyclic group optionally substituted with one or more of the following; O, S, N, halogen, or C1-4alkyl or moiety having about nine to ten ring atoms in which at least one ring is aromatic. Heteroaryl denotes a group or moiety of a monocyclic or polycyclic aromatic ring containing five or six ring atoms consisting of carbon and 1, 2, 3, or 4 heteroatoms each selected from the group consisting of non-peroxide oxygen, sulfur, and N(X) wherein X is absent or is H, O, C1-4alkyl, phenyl or benzyl.
It will be appreciated by those skilled in the art that compounds of the invention having a chiral center may exist in and be isolated in optically active and racemic forms. Some compounds may exhibit polymorphism. It is to be understood that the present invention encompasses any racemic, optically-active, polymorphic, tautomeric, or stereoisomeric form, or mixture thereof, of a compound of the invention, which possesses the useful properties described herein, it being well known in the art how to prepare optically active forms (for example, by resolution of the racemic form by recrystallization techniques, by synthesis from optically-active starting materials, by chiral synthesis, or by chromatographic separation using a chiral stationary phase) and how to determine activity using the standard tests described herein, or using other similar tests which are well known in the art.
To the extent that any pharmaceutically active compound is disclosed or claimed, it is expressly intended to include all active metabolites produced in vivo.
The carbon atom content of various hydrocarbon-containing moieties is indicated by a prefix designating the minimum and maximum number of carbon atoms in the moiety, i.e., the prefix Ci-j indicates a moiety of the integer xe2x80x9cixe2x80x9d to the integer xe2x80x9cjxe2x80x9d carbon atoms, inclusive. Thus, for example, C1-7alkyl refers to alkyl of one to seven carbon atoms, inclusive.
The compounds of the present invention are generally named according to the IUPAC or CAS nomenclature system. Abbreviations which are well known to one of ordinary skill in the art may be used (e.g. xe2x80x9cPhxe2x80x9d for phenyl, xe2x80x9cMexe2x80x9d for methyl, xe2x80x9cEtxe2x80x9d for ethyl, xe2x80x9chxe2x80x9d for hour or hours and xe2x80x9crtxe2x80x9d for room temperature).
To the extent that any numerical range is recited in connection with any aspect of the inventive compounds (e.g., dosages, treatment regimens, etc.) it expressly includes all numerals, integer and fractional, falling within the range.
Specific and preferred values listed below for groups or moieties, substituents, and ranges, are for illustration only; they do not exclude other defined values or other values within defined ranges.
2. The Invention
The present invention comprises compounds of formula I:
A compound of formula I: 
where a is a single bond or double bond, and where
R1a, R1b, R2a and R2b are each independently
(a) H, Cl, Br, I, F, CN, CF3, OCF3, OR5, CONR5R6, COR5, CO2R5, Y(CH2)mXR5 or YC(O)(CH2)mXR5, where m=0-3, Yxe2x95x90CH2, S, O, or NR6, Xxe2x95x90CH2, S, O, NR6;
(b) (CH2)pAr where p=0-3 and Ar is aryl or heteroaryl optionally substituted with one or more of the following: H, halogen, CN, NO2, OR7, CF3, OCF3, SR7, SO2R7, SO2NR7R8, NR7R8, CONR7R8, NR7COR8, NR7CONR8R9, CO2R7, COR7, or R7; or
(c) linear or branched C1-C8 alkyl, linear or branched C2-C8 alkenyl, linear or branched C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, or C3-C8 cycloalkynyl; wherein any of these groups may be optionally substituted with one or more of the following: halogen, CN, NO2, COR7, OR7, NR7R8, SR7, CO2R7, CONR7R8 or NR7COR8; and where
R3 is
(a) H, Cl, Br, I, F, CN, CF3, OCF3, alkyl, Ar, OR5, SR5, CHO, CONR5R6, COR5, CO2R5, (Y)o(CH2)nXR5, C(O)C(O)XR5, (Y)o(CH2)nC(O)XR5, C(O)(CH2)nXR5, (Y)o(CH2)nN(R6)C(O)R5, (Y)o(CH2)nN(R6)S(O)2R5, (Y)o(CH2)nN(R6)C(O)OR5, (Y)o(CH2)nN(R6)C(O)NR5R6 where o=0 or 1, n=0-3, Xxe2x95x90CH2, S, O, or NR6 and Yxe2x95x90CH2, S, O or NR6, where Ar is aryl or heteroaryl optionally substituted with one or more of the following: H, halogen, CN, NO2, OR7, CF3, OCF3, SR7, SO2R7, SO2NR7R8, NR7R8, CONR7R8, NR7COR8, NR7CONR8R9, CO2R7, COR7, or R7; or
(b) linear or branched C1-C8 alkyl, linear or branched C2-C8 alkenyl, linear or branched C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, or C3-C8 cycloalkynyl; wherein any of these groups may be optionally substituted with one or more of the following: halogen, CN, NO2, COR10, OR10, NR10R8, SR10, CO2R10, CONR10R8 or NR10COR8; and where
R4, R5 and R6 are each independently
(a) H, linear or branched C1-C8 alkyl, linear or branched C2-C8 alkenyl, linear or branched C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, or C3-C8 cycloalkynyl; wherein any of these groups other than H may be optionally substituted with one or more of the following: halogen, CN, NO2, COR10, OR10, NR10R11, SR10, CO2R10, CONR10R11 or NR10COR11; or where R5 and R6 are linked to form a 3 to 8 member ring; or
(b) (CH2)pAr where p=0-3 and Ar is aryl or heteroaryl optionally substituted with one or more of the following: H, halogen, CN, NO2, OR7, CF3, OCF3, SR7, SO2R7, SO2NR7R8, NR7R8, CONR7R8, NR7COR8, NR7CONR8R9, CO2R7, COR7, or R7; and where
R7, R8, and R9 are each independently
(a) H, linear or branched C1-C8 alkyl, linear or branched C2-C8 alkenyl, linear or branched C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, or C3-C8 cycloalkynyl groups, wherein any of these groups other than H may be optionally substituted with halogen, CN, NO2, COR10, OR10, NR10R11, SR10, CO2R10, CONR10R11, NR10COR11, NR10CONR11R12, or where R7, R8, or R9 are linked to form a ring; or
(b) (CH2)pAr where p=0-3 and Ar is aryl or heteroaryl optionally substituted with one or more of the following: H, halogen, CN, NO2, OR10, CF3, OCF3, SR10, SO2R10, SO2NR10R11, NR10R11, CONR10R11, NR10COR11, NR10CONR11R12, CO2R10, COR10, or R10; and where
R10, R11 and R12 are each independently H, linear or branched C1-C8 alkyl, linear or branched C2-C8 alkenyl, linear or branched C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, or C3-C8 cycloalkynyl;
or a stereoisomer or pharmaceutically acceptable salt thereof.
Compounds of this formula are 5-HT receptor ligands, and as such may be useful in treating animals (including humans, food animals, companion animals and other animals) against diseases and disorders of the central nervous system.
In particularly preferred embodiments, R1a, R1b, R2a, R2b and R4 are H and R3 is selected from either H, xe2x80x94C(O)C(O)XAr, xe2x80x94CH2C(O)XAr or xe2x80x94C(O)CH2XAr where X and Ar are as defined above. Even more preferred embodiments comprise the above definition where X is CH2, S, O, or NR6 and Ar is phenyl or heteroaryl optionally substituted with one or more of the following: H, halogen, CN, NO2, OR7, CF3, OCF3, SR7, SO2R7, NR7R8, CONR7R8, COR7, or R7 where R7 and R8 are each independently H, linear, branched or cyclic C1-C8 alkyl, alkenyl, or alkynyl groups, or (CH2)pPh where p=0-3.
The names of compounds falling within the scope of the present invention include, but are not limited to the following:
2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole hydrochloride
8-bromo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole hydrochloride
2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole-11-carbaldehyde
2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide
2,2,2-trifluoro-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-1-ethanoe
11-methyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole hydrochloride
11-chloro-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole hydrochloride
2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole-11-carbonitrile
8-bromo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole-11-carbaldehyde
1-(8-bromo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-2,2,2-trifluoro-1-ethanone
2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole-11-carboxamide
1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-1-ethanone hydrochloride
3-methyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
3-ethyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
3-benzyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
10-methoxy-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole hydrochloride
ethyl 2-(3-benzyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-2-oxoacetate
3-propyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole hydrochloride
2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-1-ethanamine
2-(3-benzyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-1-ethanol
3-benzyl-11-(2-phenoxyethyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
11-(2-phenoxyethyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
3-benzyl-11-[2-(2-methoxyphenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
3-benzyl-11-[2-(2-fluorophenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
3-benzyl-11-[2-(8-quinolinyloxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-1-ethanol
3-benzyl-11-[2-(2-methoxy-4-methylphenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
3-benzyl-11-[2-(2-fluoro-6-methoxyphenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
11-[2-(2-methoxyphenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
11-[2-(2-methoxyphenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole hydrochloride
11-[2-(2-fluorophenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
11-[2-(2-methoxy-4-methylphenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
11-[2-(2-fluoro-6-methoxyphenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
3-benzyl-11-[2-(2-chlorophenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
3-benzyl-11-[2-(4-bromo-2-methoxyphenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
N-benzyl-2-(3-benzyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-1-ethanamine
11-[2-(2-chlorophenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
11-[2-(4-bromo-2-methoxyphenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
2-phenoxy-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-1-ethanone
N-(4-methoxyphenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide
4-methoxy-N-[2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)ethyl]aniline dihydrochloride
2-hydroxy-N-(4-methoxyphenyl)-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide
2-(2-methoxyphenoxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-1-ethanone
2-(4-bromo-2-methoxyphenoxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-1-ethanone
N-(4-methoxyphenyl)-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide
2-(4-methoxyanilino)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-1-ethanone dihydrochloride
N-(2,4-difluorophenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide
N-(3-chloro-4-methoxyphenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide
2-oxo-N-phenyl-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide
N-(2-naphthyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide
N-(2,4-difluorophenyl)-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide
8-phenyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,4-dichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-fluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-chlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-chlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-[2-chloro-4-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,4-dimethylphenyl)-2,3,4,5tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-chloro-4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-isopropylphenyl)-2,3,4,5tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-butylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(5-fluoro-4-methoxy-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-methoxy-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-[2-chloro-4-(trifluoromethoxy)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,4,5-trimethylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(3-chlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-chloro-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,5-dichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-isopropyl-2-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,6-dichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,6-difluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-[4-methoxy-2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-[2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-pyridinyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-furyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)benzenethiol
8-(2,3-dichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-ethylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,4-dimethoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(3-chloro-2-fluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-[4-(methylsulfanyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
4-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)benzonitrile
8-[3-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-naphthyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
1-[4-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)phenyl]ethanone
N-[3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)phenyl]acetamide
8-(2,3-dimethylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(5-fluoro-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-fluoro-5-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(5-fluoro-2-methoxylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(3-chloro-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(3-nitrophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-nitrophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-chloro-3-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-methoxylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-ethoxy-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-fluoro-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-chloro-6-fluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-[2-chloro-4-(difluoromethoxy)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-[4-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-[4-(trifluoromethoxy)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(6-fluoro-2,4-dimethoxylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-[6-fluoro-2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-[2-(methylsulfanyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,4,6-trifluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,4,6-trichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,6-dichloro-4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,3,4-trifluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-chloro-2,6-difluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,3,4,6-tetrafluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,3,4,5,6-pentafluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-[2,6-di(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-[2-(trifluoromethoxy)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-[4-ethoxy-2-(trifluoromethoxy)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-[4-isopropoxy-2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-[4-chloro-2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-[4-fluoro-2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-[2-chloro-4-ethoxyphenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-[2-chloro-4-isopropoxyphenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-ethyl-4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)benzaldehyde
8-[4-methoxy-2-(1-hydroxyethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-[4-methoxy-2-(1-methoxyethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
1-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)phenyl]ethanone
[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)phenyl]methanol
8-[4-methoxy-2-(methoxymethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
1-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)phenyl]-1-propanol
1-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)phenyl]-1-propanone
methyl (2Z)-3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)phenyl]-2-propanoate
methyl 3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)phenyl]propanoate
(2Z)-3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)phenyl]-2-propen-1-ol
methyl (2E)-3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)phenyl]-2-propenoate
(2E)-3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)phenyl]-2-propen-1-ol
8-[4-methoxy-2-(2-methoxyethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-fluoro-4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-chloro-4-fluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-benzyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-fluorobenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(3-fluorobenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-fluorobenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(3-methoxybenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-ylmethyl)phenol
8-(2-methoxybenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-ylmethyl)phenol
methyl 2-methoxy-6-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)benzoate
3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)benzonitrile
3-methyl-4-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)benzonitrile
2-methyl-3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)benzonitrile
2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)benzonitrile
3-trifluoromethyl-4-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)benzonitrile
3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)benzaldehyde
[3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)phenyl]methanol
8-[3-(methoxymethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
N,N-dimethyl[3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)phenyl]methanamine
2-fluoro-5-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)benzonitrile
2-fluoro-5-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)benzamide
8-phenyl-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,4-dichlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-fluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-chlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-chlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-[2-chloro-4-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,4-dimethylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-chloro-4-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-isopropylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-butylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(5-fluoro-4-methoxy-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-methoxy-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-[2-chloro-4-(trifluoromethoxy)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,4,5-trimethylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(3-chlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-chloro-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,5-dichlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-isopropyl-2-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,6-dichlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,6-difluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-[4-methoxy-2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-[2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-pyridinyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-furyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)benzenethiol
8-(2,3-dichlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-ethylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,4-dimethoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(3-chloro-2-fluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-[4-(methylsulfanyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
4-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)benzonitrile
8-[3-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-naphthyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
1-[4-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)phenyl]ethanone
N-[3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)phenyl]acetamide
8-(2,3-dimethylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(5-fluoro-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-fluoro-5-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(5-fluoro-2-methoxylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(3-chloro-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(3-nitrophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-nitrophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-chloro-3-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-ethoxy-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-fluoro-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-chloro-6-fluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-[2-chloro-4-(difluoromethoxy)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-[4-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-[4-(trifluoromethoxy)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(6-fluoro-2,4-dimethoxylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-[6-fluoro-2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-[2-(methylsulfanyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,4,6-trifluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,4,6-trichlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,6-dichloro-4-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,3,4-trifluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-chloro-2,6-difluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,3,4,6-tetrafluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,3,4,5,6-pentafluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-[2,6-di(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-[2-(trifluoromethoxy)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-[4-ethoxy-2-(trifluoromethoxy)phenyl]-2,3,4,5,11,11 a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-[4-isopropoxy-2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-[4-chloro-2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-[4-fluoro-2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-[2-chloro-4-ethoxyphenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-[2-chloro-4-isopropoxyphenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-ethyl-4-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)benzaldehyde
8-[4-methoxy-2-(1-hydroxyethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-[4-methoxy-2-(1-methoxyethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
1-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)phenyl]ethanol
[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)phenyl]methanol
8-[4-methoxy-2-(methoxymethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
1-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)phenyl]-1-propanol
1-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)phenyl]-1-propanone
methyl (2Z)-3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)phenyl]-2-propenoate
methyl 3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)phenyl]propnoate
(2Z)-3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)phenyl]-2-propen-1-ol
methyl (2E)-3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)phenyl]-2-propenoate
(2E)-3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)phenyl]-2-propen-1-ol
8-[4-methoxy-2-(2-methoxyethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-fluoro-4-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-chloro-4-fluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-benzyl-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-fluorobenzyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(3-fluorobenzyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-fluorobenzyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(3-methoxybenzyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-ylmethyl)phenol
8-(2-methoxybenzyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-ylmethyl)phenol
methyl 2-methoxy-6-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)benzoate
3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)benzonitrile
3-methyl-4-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)benzonitrile
2-methyl-3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)benzonitrile
2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)benzonitrile
3-trifluoromethyl-4-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)benzonitrile
3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)benzaldehyde
[3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)phenyl]methanol
8-[3-(methoxymethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
N,N-dimethyl[3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)phenyl]methanamine
2-fluoro-5-(2,3,4,5,11,11a-hexahydro-1H -[1,4]diazepino[1,7-a]indol-8-yl)benzonitrile
2-fluoro-5-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)benzamide
7-phenyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,4-dichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-fluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-chlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-chlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-[2-chloro-4-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,4-dimethylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-chloro-4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-isopropylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-butylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(5-fluoro-4-methoxy-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-methoxy-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-[2-chloro-4-(trifluoromethoxy)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,4,5-trimethylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(3-chlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-chloro-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,5-dichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7(4-isopropyl-2-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,6-dichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,6-difluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-[4-methoxy-2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-[2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-pyridinyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-furyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)benzenethiol
7-(2,3-dichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-ethylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,4-dimethoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(3-chloro-2-fluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-[4-(methylsulfanyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
4-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)benzonitrile
7-[3-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-naphthyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
1-[4-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)phenyl]ethanone
N-[3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)phenyl]acetamide
7-(2,3-dimethylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(5-fluoro-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-fluoro-5-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(5-fluoro-2-methoxylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(3-chloro-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(3-nitrophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-nitrophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-chloro-3-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-methoxylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-ethoxy-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[14]diazepino[1,7-a]indole
7-(4-fluoro-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-chloro-6-fluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-[2-chloro-4-(difluoromethoxy)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-[4-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-[4-(trifluoromethoxy)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(6-fluoro-2,4-dimethoxylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-[6-fluoro-2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-[2-(methylsulfanyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,4,6-trifluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,4,6trichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,6-dichloro-4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,3,4-trifluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-chloro-2,6-difluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,3,4,6-tetrafluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,3,4,5,6-pentafluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-[2,6-di(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-[2-(trifluoromethoxy)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-[4-ethoxy-2-(trifluoromethoxy)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-[4-isopropoxy-2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-[4-chloro-2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-[4-fluoro-2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-[2-chloro-4-ethoxyphenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-[2-chloro-4-isopropoxyphenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-ethyl-4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)benzaldehyde
7-[4-methoxy-2-(1-hydroxyethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-[4-methoxy-2-(1-methoxyethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
1-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)phenyl]ethanone
[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)phenyl]methanol
7-[4-methoxy-2-(methoxymethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
1-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)phenyl]-1-propanol
1-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)phenyl]-1-propanoate
methyl (2Z)-3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)phenyl]-2-propenoate
methyl 3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)phenyl]propanoate
(2Z)-3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)phenyl]-2-propen-1-ol
methyl (2E)-3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)phenyl]-2-propenoate
(2E)-3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)phenyl]-2-propen-1-ol
7-[4-methoxy-2-(2-methoxyethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-fluoro-4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-chloro-4-fluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-benzyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-fluorobenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(3-fluorobenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-fluorobenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(3-methoxybenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-ylmethyl)phenol
7-(2-methoxybenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-ylmethyl)phenol
methyl 2-methoxy-6-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)benzoate
3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)benzonitrile
3-methyl-4-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)benzonitrile
2-methyl-3-(2,3,4,5-tetrahydro-1H -[1,4]diazepino[1,7-a]indol -7-yl)benzonitrile
2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)benzonitrile
3-trifluoromethyl-4-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)benzonitrile
3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)benzaldehyde
[3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)phenyl]methanol
7-[3-(methoxymethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
N,N-dimethyl[3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)phenyl]methanamine
2-fluoro-5-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)benzonitrile
2-fluoro-5-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)benzamide
7-phenyl-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,4-dichlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-fluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-chlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-chlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-[2-chloro-4-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,4-dimethylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-chloro-4-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-isopropylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-butylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(5-fluoro-4-methoxy-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-methoxy-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-[2-chloro-4-(trifluoromethoxy)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,4,5-trimethylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(3-chlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-chloro-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,5-dichlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-isopropyl-2-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,6-dichlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,6-difluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-[4-methoxy-2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-[2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-pyridinyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-furyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)benzenethiol
7-(2,3-dichlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-ethylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,4-dimethoxyphenyl)2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(3-chloro-2-fluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-[4-(methylsulfanyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
4-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)benzonitrile
7-[3-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-naphthyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
1-[4-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)phenyl]ethanone
N-[3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)phenyl]acetamide
7-(2,3-dimethylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(5-fluoro-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-fluoro-5-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(5-fluoro-2-methoxylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(3-chloro-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(3-nitrophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-nitrophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-chloro-3-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-methoxylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-ethoxy-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-fluoro-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-chloro-6-fluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-[2-chloro-4-(difluoromethoxy)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-[4-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-[4-(trifluoromethoxy)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(6-fluoro-2,4-dimethoxylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-[6-fluoro-2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-[2-(methylsulfanyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,4,6-trifluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,4,6-trichlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,6-dichloro-4-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,3,4-trifluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-chloro-2,6-difluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,3,4,6-tetrafluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,3,4,5,6-pentafluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-[2,6-di(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-[2-(trifluoromethoxy)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-[4-ethoxy-2-(trifluoromethoxy)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-[4-isopropoxy-2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-[4-chloro-2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-[4-fluoro-2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-[2-chloro-4-ethoxyphenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-[2-chloro-4-isopropoxyphenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-ethyl-4-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)benzaldehyde
7-[4-methoxy-2-(1-hydroxyethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-[4-methoxy-2-(1-methoxyethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
1-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)phenyl]ethanone
[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)phenyl]methanol
7-[4-methoxy-2-(methoxymethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
1-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)phenyl]-1-propanol
1-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)phenyl]-1-propanone
methyl (2Z)-3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)phenyl]-2-propenoate
methyl 3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)phenyl]propanoate
(2Z)-3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)phenyl]-2-propen-1-ol
methyl (2E)-3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)phenyl]-2-propenoate
(2E)-3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)phenyl]-2-propen-1-ol
7-[4-methoxy-2-(2-methoxyethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-fluoro-4-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-chloro-4-fluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-benzyl-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-fluorobenzyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(3-fluorobenzyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-fluorobenzyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(3-methoxybenzyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7-ylmethyl)phenol
7-(2-methoxybenzyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7-ylmethyl)phenol
methyl 2-methoxy-6-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)benzoate
3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)benzonitrile
3-methyl-4-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)benzonitrile
2-methyl-3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)benzonitrile
2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)benzonitrile
3-trifluoromethyl-4-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol -7-yl)benzonitrile
3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)benzaldehyde
[3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)phenyl]methanol
7-[3-(methoxymethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
N,N-dimethyl[3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)phenyl]methanamine
2-fluoro-5-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol -7-yl)benzonitrile
2-fluoro-5-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)benzamide
9-phenyl-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,4-dichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-fluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-chlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2-chlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-[2-chloro-4-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,4-dimethylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2-chloro-4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-isopropylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-butylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(5-fluoro-4-methoxy-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-methoxy-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-[2-chloro-4-(trifluoromethoxy)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,4,5-trimethylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(3-chlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-chloro-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,5-dichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-isopropyl-2-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,6-dichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,6-difluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-[4-methoxy-2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-[2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-pyridinyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2-furyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)benzenethiol
9-(2,3-dichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-ethylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,4-dimethoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(3-chloro-2-fluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-[4-(methylsulfanyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
4-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)benzonitrile
9-[3-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2-naphthyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
1-[4-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)phenyl]ethanone
N-[3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)phenyl]acetamide
9-(2,3-dimethylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(5-fluoro-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2-fluoro-5-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(5-fluoro-2-methoxylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(3-chloro-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(3-nitrophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2-nitrophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2-chloro-3-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2-methoxylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-ethoxy-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-fluoro-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2-chloro-6-fluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-[2-chloro-4-(difluoromethoxy)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-[4-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-[4-(trifluoromethoxy)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(6-fluoro-2,4-dimethoxylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-[6-fluoro-2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-[2-(methylsulfanyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,4,6-trifluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,4,6-trichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,6-dichloro-4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,3,4-trifluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-chloro-2,6-difluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,3,4,6-tetrafluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,3,4,5,6-pentafluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-[2,6-di(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-[2-(trifluoromethoxy)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-[4-ethoxy-2-(trifluoromethoxy)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-[4-isopropoxy-2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-[4-chloro-2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-[4-fluoro-2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-[2-chloro-4-ethoxyphenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-[2-chloro-4-isopropoxyphenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2-ethyl-4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[14]diazepino[1,7-a]indole
5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)benzaldehyde
9-[4-methoxy-2-(1-hydroxyethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-[4-methoxy-2-(1-methoxyethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
1-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)phenyl]ethanone
[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)phenyl]methanol
9-[4-methoxy-2-(methoxymethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
1-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)phenyl]-1-propanol
1-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)phenyl]-1-propanone
methyl (2Z)-3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)phenyl]-2-propenoate
methyl 3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)phenyl]propanoate
(2Z)-3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)phenyl]-2-propen-1-ol
methyl (2E)-3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)phenyl]-2-propenoate
(2E)-3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)phenyl]-2-propen-1-ol
9-[4-methoxy-2-(2-methoxyethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2-fluoro-4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2-chloro-4-fluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-benzyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2-fluorobenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(3-fluorobenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-fluorobenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(3-methoxybenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-ylmethyl)phenol
9-(2-methoxybenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-ylmethyl)phenol
methyl 2-methoxy-6-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)benzoate
3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)benzonitrile
3-methyl-4-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)benzonitrile
2-methyl-3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)benzonitrile
2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)benzonitrile
3-trifluoromethyl-4-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)benzonitrile
3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)benzaldehyde
[3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)phenyl]methanol
9-[3-(methoxymethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
N,N-dimethyl[3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)phenyl]methanamine
2-fluoro-5-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)benzonitrile
2-fluoro-5-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)benzamide
9-phenyl-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,4-dichlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-fluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-chlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2-chlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-[2-chloro-4-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,4-dimethylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2-chloro-4-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-isopropylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-butylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(5-fluoro-4-methoxy-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-methoxy-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-[2-chloro-4-(trifluoromethoxy)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,4,5-trimethylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(3-chlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-chloro-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,5-dichlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-isopropyl-2-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,6-dichlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,6-difluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-[4-methoxy-2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-[2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-pyridinyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2-furyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)benzenethiol
9-(2,3-dichlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-ethylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,4-dimethoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(3-chloro-2-fluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-[4-(methylsulfanyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
4-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)benzonitrile
9-[3-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2-naphthyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
1-[4-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)phenyl]ethanone
N-[3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)phenyl]acetamide
9-(2,3-dimethylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(5-fluoro-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2-fluoro-5-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(5-fluoro-2-methoxylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(3-chloro-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(3-nitrophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2-nitrophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2-chloro-3-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2-methoxylphenyl)-2,3,4,5,11,11a-hexahydro-1H 1-[1,4]diazepino[1,7-a]indole
9-(4-ethoxy-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-fluoro-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2-chloro-6-fluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-[2-chloro-4-(difluoromethoxy)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-[4-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-[4-(trifluoromethoxy)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(6-fluoro-2,4-dimethoxylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-[6-fluoro-2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-[2-(methylsulfanyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,4,6-trifluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,4,6-trichlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,6-dichloro-4-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,3,4-trifluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-chloro-2,6-difluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,3,4,6-tetrafluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,3,4,5,6-pentafluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-[2,6-di(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-[2-(trifluoromethoxy)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-[4-ethoxy-2-(trifluoromethoxy)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-[4-isopropoxy-2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-[4-chloro-2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-[4-fluoro-2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-[2-chloro-4-ethoxyphenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-[2-chloro-4-isopropoxyphenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2-ethyl-4-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)benzaldehyde
9-[4-methoxy-2-(1-hydroxyethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-[4-methoxy-2-(1-methoxyethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
1-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)phenyl]ethanone
[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)phenyl]methanol
9-[4-methoxy-2-(methoxymethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
1-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)phenyl]-1-propanol
1-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)phenyl]-1-propanone
methyl (2Z)-3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)phenyl]-2-propenoate
methyl 3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)phenyl]propanoate
(2Z)-3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)phenyl]-2-propen-1-ol
methyl (2E)-3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)phenyl]-2-propenoate
(2E)-3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)phenyl]-2-propen-1-ol
9-[4-methoxy-2-(2-methoxyethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2-fluoro-4-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2-chloro-4-fluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-benzyl-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2-fluorobenzyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(3-fluorobenzyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-fluorobenzyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(3-methoxybenzyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-ylmethyl)phenol
9-(2-methoxybenzyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-ylmethyl)phenol
methyl 2-methoxy-6-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)benzoate
3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)benzonitrile
3-methyl-4-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)benzonitrile
2-methyl-3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)benzonitrile
2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)benzonitrile
3-trifluoromethyl-4-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)benzonitrile
3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)benzaldehyde
[3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)phenyl]methanol
9-[3-(methoxymethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
N,N-dimethyl[3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)phenyl]methanamine
2-fluoro-5-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)benzonitrile, and
2-fluoro-5-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)benzamide.
Other compounds which technically are not within the scope of formula I but are considered to be within the scope of the instant invention include:
tert-butyl 1,2,4,5-tertrahydro-3H[1,4]diazepino[1,7-a]-indole-3-carboxylate;
11[(E)-2-nitroethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino-[1,7-a]indole;
3-(trifluoroacetyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino-[1,7-a]indole; and
2-bromo-1-[3-(trifluoroacetyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1-7-a]indole-11-yl]ethanone.
The following describe the preparation of compounds of the present invention. All of the starting materials are prepared by procedures described herein or by procedures that would be well known to one of ordinary skill in organic chemistry.
Compounds of Formula I where R1a, R1b, R2a, R2b, R4, and R3=H can be prepared by reactions outlined in Chart A1. Step 1 involves the reaction of a 2-nitrophenylacetic acid derivative with carbonyl diimidazole followed by the addition of a magnesium salt of ethylhydrogen malonate to provide compound 1. In Step 2, treatment of the xcex2-ketoester with TiCl3 in the presence of water and acetone reduces the nitro group followed by spontaneous dehydrative cyclization with the ketone moiety to provide 3-indoleacetic acid derivatives 2. This dehydrative cyclization is also accomplished under heterogeneous palladium catalyzed hydrogenylitic conditions. In Step 3, reduction of the indole to the corresponding indoline 3 is achieved by the action of NaCNBH3 in the presence of an acid such as acetic acid or trifluoroacetic acid. In Step 4, the aniline moiety is alkylated with 1,2-dibromoethane in the presence of base and a suitable solvent such as CH3CN or N-methylpyrrolidinone to afford trisubstituted amine derivatives 4. In Step 5, a second annulation occurs by the reaction of 4 with a primary amine of formula R4NH2, where R4 is as defined above, to provide azepinones 5. In Step 6, the carbonyl group of compound 5 is reduced by reaction with a reducing agent such as diisobutylaluminum hydride in a suitable solvent such as tetrahydrofuran or toluene to yield azepines 6. Finally, oxidation of indolines 6 to the corresponding indoles 7 is achieved by the action of an oxidant such as 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) in the presence of a suitable solvent such as dixoane (Examples 1-3).
Additionally, compounds of Formula I where R1a, R1b, R2a, R2b, R3 and R4 are as defined above and bond a is a single or double bond can be prepared by reactions outlined in Chart G. Step 1 involves the reaction of 20 (where X can be but is not limited to I, Br, Cl, triflate, organotin, and organoboron) under various catalytic transition metal coupling procedures. These procedures can be performed by one skilled in the art of organic chemistry and include, but are not limited to, the Suzuki coupling (for a review see Snieckus, V.; Chem. Rev.; 90; 897; 1990), the Stille coupling (for a review see Beletzkaya, I. P.; J. Organomet. Chem.; 250; 551; 1983), the Heck coupling (for a review see de Meijere, A. and Meyer, F. E.; Angew. Chem. Int. Ed. Engl.; 33; 2379; 1994), heteroatom carbon coupling reactions (for a review see Buchwald, S. L. and Yang, B. H.; J. Organomet. Chem.; 576; 125; 1999), and carbonylation reactions (for an example see Heck, R. F.; Schoenberg, A.; Bartoletti, I.; J. Org. Chem.; 39; 3318; 1974).
The present invention also resides in the production of compounds wherein R3 of Formula I is as defined above except for hydrogen. To obtain compounds having specific R3 groups other than hydrogen, 2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole is reacted with appropriate reactants using standard organic chemical synthesis procedures as would be well understood in the art. Examples of such standard procedures are shown in Charts B-E.
For example, Chart B illustrates the preparation of compounds where R1a, R1b, R2a, R2b and R4 are H and R3 is xe2x80x94C(O)C(O)XR5, where X and R5 are as defined above.
In step 1, a N-protected derivative 8 is reacted with oxalyl chloride in dichloromethane at reduced temperatures to produce the corresponding xcex1-keto acid chloride. This uncharacterized intermediate is reacted with various XR5 in the presence of a tertiary amine base such as triethyl amine or diisopropylethyl amine and an appropriate solvent such as dichloromethane or toluene. Upon consumption of the xcex1-keto acid chloride, the protecting group is cleaved under standard deprotection conditions such as trifluoroacetic acid for the tert-butyl carbamate group or alkaline alcoholic conditions for the trifluoro acetamide group to afford xcex1-ketoamide products 9. This sequence can be carried out with non-critical variations utilizing parallel synthetic techniques and employing polymer supported reagents as reactants, scavengers, and capture-release reagents to produce libraries of final products.
Chart C illustrates the preparation of compounds where R1a, R1b, R2a, R2b and R4 are H and R3 is xe2x80x94CH2C(O)XR5, where X and R5 are as defined above. In step 1, products 9 (Chart B, step 1) are reacted in an appropriate solvent such as 1,2-dichloroethane with a reducing agent such as triethyl silane under acidic conditions and elevated temperatures to afford the selectively reduced products 10.
The production of compounds where R1a, R1b, R2a, R2b and R4 are H and R3 is xe2x80x94CH2CH2XR5, where X and R5 are as defined above is depicted in Chart D. In step 1, 3-benzyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole is reacted with oxalyl chloride in an appropriate solvent such as diethyl ether or dichloromethane at reduced temperatures to give an intermediate xcex1-keto acid chloride that is reacted with ethanol to afford compound 12. Reduction of the dicarbonyl moiety is achieved in a two-step procedure involving initial reduction with lithium aluminum hydride in an appropriate solvent such as tetrahydrofuran to the corresponding diol followed by reduction of the secondary alcohol by the action of triethyl silane under acidic conditions in an appropriate solvent such as dichloromethane to afford 13. In step 3, substitution with XR5 as defined above is accomplished under Mitsunobu reaction conditions or by functionalization of the terminal alcohol moiety of 13 to a suitable leaving group such as mesylate followed by nucleophilic displacement to give compounds 14. Finally, debenzylation of the azepino nitrogen is accomplished by palladium catalyzed hydrogenolysis in the presence of a hydrogen source such as ammonium formate to afford compounds 15. Alternatively, conversion of 14 to the corresponding trichloroethyl carbamate derivative followed by cleavage of the newly installed protecting group by the action of zinc in acetic acid affords compounds 15. This sequence can be carried out with non-critical variations utilizing parallel synthetic techniques and employing polymer supported reagents as reactants, scavengers, and capture-release reagents to produce libraries of final products.
Chart E illustrates the preparation of compounds where R1a, R1b, R2a, R2b and R4 are H and R3 is xe2x80x94C(O)CH2XR5, where X and R5 are as defined above. In step 1, protected intermediate 8 is reacted with bromoacetyl bromide in the presence of a Lewis acid such as aluminum trichloride and an appropriate solvent such as dichloromethane to give 16. This xcex1-bromo ketone is substituted with XR5 as defined above by alkylation in the presence of a suitable base such as potassium carbonate and solvent such as acetonitrile. Upon consumption of the xcex1-keto bromide, the protecting group is cleaved under standard deprotection conditions such as trifluoroacetic acid for the tert-buyl carbamate group or alkaline alcoholic conditions for the trifluoro acetamide group to afford products 17. This sequence can be carried out with non-critical variations utilizing parallel synthetic techniques and employing polymer supported reagents as reactants, scavengers, and capture-release reagents to produce libraries of final products.
The present invention also resides in the production of compounds wherein bond a is a single bond of Formula I and where R1a, R1b, R2a, R2b, R3, and R4 are as defined above. To obtain compounds having bond a as a single bond, derivatives of 2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a] are reacted with appropriate reactants using standard organic chemical synthesis procedures as would be well understood in the art.
Chart F illustrates the preparation of compounds I where bond a is a single bond and R1, R2, R3, and R4 are as defined above. In step 1, the indole products 18 are reduced by the action of a reducing reagent such as sodium cyanoborohydride or triethylsilane in acidic conditions to afford the corresponding indolines 19. Alternatively, reduction can be achieved by catalytic hydrogenation under elevated pressures of hydrogen in the presence of a metal catalyst such as palladium, platinum, rhodium, or nickel, (for an overview of indole reductions to indolines see Sundberg, R. J.; Indoles; Academic Press, 145; 1996).
The above compounds are useful in treating diseases or disorders of the central nervous system occurring in animals, preferably mammals. Typically, the mammal is a human being, but the inventive compounds can be used to treat other animals such as food animals (e.g., cows, pigs, sheep, goats, deer, poultry, etc.), companion animals (e.g., dogs, cats, horses, birds and fish), or other animals. The compounds may be administered in their native form, or, more typically, with a pharmaceutically acceptable excipient. The compounds may also be administered in acid or basic salt forms.
In cases where compounds are sufficiently basic or acidic to form stable nontoxic acid or base salts, administration of the compounds as salts may be appropriate. Examples of pharmaceutically acceptable salts are organic acid addition salts formed with acids which form a physiological acceptable anion, for example, tosylate, methanesulfonate, acetate, citrate, malonate, tartarate, succinate, benzoate, ascorbate, xcex1-ketoglutarate, maleate, fumarate, benzenesulfonate and xcex1-glycerophosphate. Suitable inorganic salts may also be formed, including hydrobromide, hydrochloride, sulfate, nitrate, bicarbonate, and carbonate salts.
Pharmaceutically acceptable salts may be obtained using standard procedures well known in the art, for example by reacting a sufficiently basic compound such as an amine with a suitable acid affording a physiologically acceptable anion. Alkali metal (for example, sodium, potassium or lithium) or alkaline earth metal (for example calcium) salts of carboxylic acids can also be made.
Compounds of the present invention can conveniently be administered in a pharmaceutical composition containing the compound in combination with a suitable excipient. Such pharmaceutical compositions can be prepared by methods and contain excipients which are well known in the art. A generally recognized compendium of such methods and ingredients is Remington""s Pharmaceutical Sciences by E. W. Martin (Mark Publ. Co., 15th Ed., 1975). To the extent necessary for completion, this reference is hereby incorporated by reference. The compounds and compositions of the present invention can be administered parenterally (for example, by intravenous, intraperitoneal or intramuscular injection), topically, nasally, orally, or rectally.
For oral therapeutic administration, the active compound may be combined with one or more excipients and used in the form of ingestible tablets, buccal tablets, troches, capsules, elixirs, suspensions, syrups, wafers, and the like. Such compositions and preparations should contain at least 0.1% of active compound. The percentage of the compositions and preparations may, of course, be varied and may conveniently be between about 2 to about 60% of the weight of a given unit dosage form. The amount of active compound in such therapeutically useful compositions is such that an effective dosage level will be obtained.
The tablets, troches, pills, capsules, and the like may also contain the following: binders such as gum tragacanth, acacia, corn starch or gelatin; excipients such as dicalcium phosphate; a disintegrating agent such as corn starch, potato starch, alginic acid and the like; a lubricant such as magnesium stearate; and a sweetening agent such as sucrose, fructose, lactose or aspartame or a flavoring agent such as peppermint, oil of wintergreen, or cherry flavoring. The above listing is merely representative and one skilled in the art could envision other binders, excipients, sweetening agents and the like. When the unit dosage form is a capsule, it may contain, in addition to materials of the above type, a liquid carrier, such as a vegetable oil or a polyethylene glycol. Various other materials may be present as coatings or to otherwise modify the physical form of the solid unit dosage form. For instance, tablets, pills, or capsules may be coated with gelatin, wax, shellac or sugar and the like. A syrup or elixir may contain the active compound, sucrose or fructose as a sweetening agent, methyl and propylparabens as preservatives, a dye and flavoring such as cherry or orange flavor. Of course, any material used in preparing any unit dosage form should be pharmaceutically acceptable and substantially non-toxic in the amounts employed. In addition, the active compound may be incorporated into sustained-release preparations and devices including, but not limited to, those relying on osmotic pressures to obtain a desired release profile (e.g., the OROS drug delivery devices as designed and developed by Alza Corporation).
The compounds or compositions can also be administered intravenously or intraperitoneally by infusion or injection. Solutions of the active compound or its salts can be prepared in water, optionally mixed with a nontoxic surfactant. Dispersions can also be prepared in glycerol, liquid polyethylene glycols, triacetin, and mixtures thereof and in oils. Under ordinary conditions of storage and use, these preparations contain a preservative to prevent the growth of microorganisms.
Pharmaceutical dosage forms suitable for injection or infusion can include sterile aqueous solutions or dispersions or sterile powders comprising the active ingredient which are adapted for the extemporaneous preparation of sterile injectable or infusible solutions or dispersions, optionally encapsulated in liposomes. In all cases, the ultimate dosage form should be sterile, fluid and stable under the conditions of manufacture and storage. The liquid carrier or vehicle can be a solvent or liquid dispersion medium comprising, for example, water, ethanol, a polyol (for example, glycerol, propylene glycol, liquid polyethylene glycols, and the like), vegetable oils, nontoxic glyceryl esters, and suitable mixtures thereof. The proper fluidity can be maintained, for example, by the formation of liposomes, by the maintenance of the required particle size in the case of dispersions or by the use of surfactants. The prevention of the action of microorganisms can be brought about by various antibacterial and antifungal agents, for example, parabens, chlorobutanol, phenol, sorbic acid, thimerosal, and the like. In many cases, it will be preferable to include isotonic agents, for example, sugars, buffers or sodium chloride. Prolonged absorption of the injectable compositions can be brought about by the use in the compositions of agents delaying absorption, for example, aluminum monostearate and gelatin.
Sterile injectable solutions can be prepared by incorporating the active compound in the required amount in the appropriate solvent with various of the other ingredients enumerated above, as required, followed by filter sterilization. In the case of sterile powders for the preparation of sterile injectable solutions, the preferred methods of preparation are vacuum drying and the freeze drying techniques, which yield a powder of the active ingredient plus any additional desired ingredient present in the previously sterile-filtered solutions. Sterilization of the powders may also be accomplished through irradiation and aseptic crystallization methods. The sterilization method selected is the choice of the skilled artisan.
For topical administration, the present compounds may be applied in pure form, i.e., when they are liquids. However, it will generally be desirable to administer them to the skin as compositions or formulations, in combination with a dermatologically acceptable carrier, which may be a solid or a liquid.
Useful solid carriers include finely divided solids such as talc, clay, microcrystalline cellulose, silica, alumina and the like. Useful liquid carriers include water, alcohols or glycols or water-alcohol/glycol blends, in which the present compounds can be dissolved or dispersed at effective levels, optionally with the aid of non-toxic surfactants. Adjuvants such as fragrances and additional antimicrobial agents can be added to optimize the properties for a given use. The resultant liquid compositions can be applied from absorbent pads, used to impregnate bandages and other dressings, or sprayed onto the affected area using pump-type or aerosol sprayers. Thickeners such as synthetic polymers, fatty acids, fatty acid salts and esters, fatty alcohols, modified celluloses or modified mineral materials can also be employed with liquid carriers to form spreadable pastes, gels, ointments, soaps, and the like, for application directly to the skin of the user. To this extent, the present invention further contemplates the use of the pharmaceutically active materials in personal care compositions such as lotions, cleansers, powders, cosmetics and the like.
The compound is conveniently administered in unit dosage form; for example, containing about 0.05 mg to about 500 mg, conveniently about 0.1 mg to about 250 mg, most conveniently, about 1 mg to about 150 mg of active ingredient per unit dosage form. The desired dose may conveniently be presented in a single dose or as divided doses administered at appropriate intervals, for example, as two, three, four or more sub-doses per day. The sub-dose itself may be further divided, e.g., into a number of discrete loosely spaced administrations.
The compositions can conveniently be administered orally, sublingually, transdermally, or parenterally at dose levels of about 0.01 to about 150 mg/kg, preferably about 0.1 to about 50 mg/kg, and more preferably about 0.1 to about 10 mg/kg of mammal body weight.
For parenteral administration the compounds are presented in aqueous solution in a concentration of from about 0.1 to about 10%, more preferably about 0.1 to about 7%. The solution may contain other ingredients, such as emulsifiers, antioxidants or buffers.
The exact regimen for administration of the compounds and compositions disclosed herein will necessarily be dependent upon the needs of the individual subject being treated, the patient type (i.e., human or animal), the type of treatment and, of course, the judgment of the attending practitioner.
Generally, compounds of the invention are 5-HT ligands. The ability of a compound of the invention to act as a 5-HT receptor agonist, partial agonist or antagonist can also be determined using in vitro and in vivo assays that are known in the art. The invention provides compounds of formula I that act as either agonists, partial agonists or as antagonists of one or more 5-HT receptor subtypes.
The inventive compounds of the present invention may be useful as modulators of 5-HT receptor function. Thus, the compounds are useful for treating diseases or disorders where modulation of 5-HT receptor function is desired. This inventive composition is used to treat any of the diseases or disorders of the central nervous system. Such diseases and disorders are defined in The Diagnostic and Statistical Manual of Mental Disorders-IV (DSM-IV) (American Psychiatric Association (1995)). To the extent necessary for completion, the contents of this reference and all of the defined diseases or disorders are expressly incorporated by reference. Representative diseases or disorders include, but are not limited to the following: obesity, depression, schizophrenia, a stress related disease (e.g. general anxiety disorder), panic disorder, a phobia, obsessive compulsive disorder, post-traumatic-stress syndrome, immune system depression, incontinence, a stress induced problem with the urinary, gastrointestinal or cardiovascular system (e.g., stress incontinence), neurodegenerative disorders, autism, chemotherapy-induced vomiting, hypertension, migraine headaches, cluster headaches, sexual dysfunction in a mammal (e.g. a human), addictive disorder and withdrawal syndrome, an adjustment disorder, an age-associated learning and mental disorder, anorexia nervosa, apathy, an attention-deficit disorder due to general medical conditions, attention-deficit hyperactivity disorder, bipolar disorder, bulimia nervosa, chronic fatigue syndrome, conduct disorder, cyclothymic disorder, dysthymic disorder, fibromyalgia and other somatoform disorders, generalized anxiety disorder, an inhalation disorder, an intoxication disorder, a movement disorder (e.g., Tourette""s syndrome), oppositional defiant disorder, a pain disorder, peripheral neuropathy, post-traumatic stress disorder, premenstrual dysphoric disorder, a psychotic disorder, seasonal affective disorder, a sleep disorder, a specific developmental disorder, and selective serotonin reuptake inhibition (SSRI) xe2x80x9cpoop outxe2x80x9d syndrome. Treatment of the above diseases or disorders is accomplished by delivering a therapeutically effective amount of the inventive composition to a mammal. In most cases this will be a human being, but treatment of food animals (e.g., livestock such as cows, pigs, deer, sheep, goats and the like, and poultry) and companion animals (e.g., dogs, cats, birds, fish and horses) is expressly covered herein.
The invention is described in greater detail by the following non-limiting examples.